US4108748A - Photofinishing of cotton textiles - Google Patents
Photofinishing of cotton textiles Download PDFInfo
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- US4108748A US4108748A US05/563,257 US56325775A US4108748A US 4108748 A US4108748 A US 4108748A US 56325775 A US56325775 A US 56325775A US 4108748 A US4108748 A US 4108748A
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- United States
- Prior art keywords
- cotton
- fabric
- dmf
- acrylated
- photolyzed
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- 229920000742 Cotton Polymers 0.000 title claims abstract description 63
- 239000004753 textile Substances 0.000 title description 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims abstract description 194
- 239000004744 fabric Substances 0.000 claims abstract description 68
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000012298 atmosphere Substances 0.000 claims abstract description 4
- 238000011084 recovery Methods 0.000 claims description 29
- 230000037303 wrinkles Effects 0.000 claims description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 27
- 238000000034 method Methods 0.000 claims description 21
- 238000006467 substitution reaction Methods 0.000 claims description 19
- 238000006243 chemical reaction Methods 0.000 claims description 9
- NIXOWILDQLNWCW-UHFFFAOYSA-M acrylate group Chemical group C(C=C)(=O)[O-] NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 4
- 238000004132 cross linking Methods 0.000 claims description 4
- CERQOIWHTDAKMF-UHFFFAOYSA-M methacrylate group Chemical group C(C(=C)C)(=O)[O-] CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 4
- 238000001035 drying Methods 0.000 claims description 3
- WHQSYGRFZMUQGQ-UHFFFAOYSA-N n,n-dimethylformamide;hydrate Chemical compound O.CN(C)C=O WHQSYGRFZMUQGQ-UHFFFAOYSA-N 0.000 claims description 3
- 239000011877 solvent mixture Substances 0.000 claims description 3
- 238000005406 washing Methods 0.000 claims 2
- 241000219146 Gossypium Species 0.000 description 41
- 239000002904 solvent Substances 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 230000001143 conditioned effect Effects 0.000 description 5
- 238000006303 photolysis reaction Methods 0.000 description 5
- 230000015843 photosynthesis, light reaction Effects 0.000 description 5
- 230000000694 effects Effects 0.000 description 4
- 229920002678 cellulose Polymers 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 238000013007 heat curing Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- VHRYZQNGTZXDNX-UHFFFAOYSA-N methacryloyl chloride Chemical compound CC(=C)C(Cl)=O VHRYZQNGTZXDNX-UHFFFAOYSA-N 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 230000000135 prohibitive effect Effects 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 238000012993 chemical processing Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000001723 curing Methods 0.000 description 1
- 230000009089 cytolysis Effects 0.000 description 1
- 230000003413 degradative effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 230000000877 morphologic effect Effects 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B15/00—Preparation of other cellulose derivatives or modified cellulose, e.g. complexes
- C08B15/005—Crosslinking of cellulose derivatives
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M14/00—Graft polymerisation of monomers containing carbon-to-carbon unsaturated bonds on to fibres, threads, yarns, fabrics, or fibrous goods made from such materials
- D06M14/18—Graft polymerisation of monomers containing carbon-to-carbon unsaturated bonds on to fibres, threads, yarns, fabrics, or fibrous goods made from such materials using wave energy or particle radiation
- D06M14/20—Graft polymerisation of monomers containing carbon-to-carbon unsaturated bonds on to fibres, threads, yarns, fabrics, or fibrous goods made from such materials using wave energy or particle radiation on to materials of natural origin
- D06M14/22—Graft polymerisation of monomers containing carbon-to-carbon unsaturated bonds on to fibres, threads, yarns, fabrics, or fibrous goods made from such materials using wave energy or particle radiation on to materials of natural origin of vegetal origin, e.g. cellulose or derivatives thereof
Definitions
- This invention relates to chemical processing of cotton textiles. Specifically, this invention relates to the wet-processing of cotton fabric which has been previously chemically modified. More specifically, this invention relates to a multistep wet processing of acrylated and methacrylated cotton fabric subjecting the reacted fabric to a near ultraviolet light treatment, a photofinishing step, to form a crosslinked cotton fabric with useful durable-press properties.
- the main object of this invention is to provide a new textile wet-process method.
- a second object of this invention is to provide a chemical treatment for further enhancing the physical properties of acrylated and methacrylated cotton without using a heat cure.
- a third object of this invention is to provide a photofinishing process for initiating crosslinking reactions of acrylated and methacrylated cottons to yield textile fabrics with durable-press properties.
- the macromolecular properties of cotton are stabilized and the morphological properties of cotton are imparted a retention and recovery of initial shape and form after deformation, so that durable-press cotton fabric with high wrinkle recovery angles are produced.
- the method of this invention has as its objective the modification of the chemical structure of cotton fibers, mechanically organized into textile products and then the photofinishing of the modified products to yield an all-cotton, durable-press textile with high wrinkle recovery angles and easy care properties.
- the instant invention defines a distinct improvement in the textile, durable-press properties of all-cotton fabrics in which acrylate and methacrylate chemical derivatives of cotton cellulose fabrics are prepared and then photolyzed by near ultraviolet light to yield crosslinked, durable-press cotton fabrics with improved wrinkle recovery angles with minimum losses in breaking strengths of the chemically modified cotton fabrics.
- Cotton cellulose fabrics that had been chemically modified by reaction with acryloyl chloride or methacryloyl chloride to degrees of substitution ranging from 0.08 to 0.50 were padded with N,N-dimethylformamide, water, combinations of these two solvents ranging from 10 to 100 percent N,N-dimethylformamide and 10 to 100 percent water, or solutions of these solvents containing acrylamide ranging from 0.5 to 4 percent and then photolyzed for 30 minutes to 22 hours in nitrogen or air atmospheres at ambient temperature, about 48° C, by near ultraviolet light with a wavelength maximum of 3500 angstroms, which had been shown to yield a maximum concentration of cellulosic radicals with minimum degradative damage to the physical properties of cotton, to yield cotton fabrics with Monsanto wrinkle recovery angles (American Society for Testing and Materials, Philadelphia, Pa., test method ASTM Designation D1295-60T) as high as 331° (wet) and 285° (conditioned), as compared with wrinkle recovery angles of control fabrics of 174° (wet) and 160
- Samples of cotton fabric used were a commercial grey printcloth (about 3.2 ounces per square yard, 80 ⁇ 80 thread count) which had been enzymatically desired, alkali scoured, and peroxide bleached before use.
- two or three strips of cotton fabric about 5 to 7.5 parts, were rolled together and placed together in a container fitted with a drying tube.
- Calcium carbonate (about 6 parts), N,N-dimethylformamide (about 60 parts), and acryloyl chloride or methacryloyl chloride (3 to 10 parts) were added to the container.
- the container and its contents were heated typically in an oil bath at 100° to 110° C for the time required to give the cotton cellulose ester with the desired degree of substitution. After cooling the samples to about 25° C, they were washed in water and air-dried either in a slack condition or under tension on pin frames.
- the present invention can best be described as the acrylated and the methacrylated cotton products and processes for making these, the processes of which can be that embodiment for imparting to cotton fabrics the desirable durable press property of wrinkle recovery while retaining the natural properties of untreated cotton, and comprising:
- Samples of the acrylated or methacrylated cotton fabrics were impregnated with solvents or solutions, as indicated by padding to a wet add-on of about 180 percent. These treated samples were placed in a container in the desired atmosphere and exposed to near ultraviolet light which had about 90 percent of the intensity of the light with a wavelength of about 3500 Angstrom units, at ambient temperatures for certain specific times, ranging about from 30 minutes to 22 hours, in a nitrogen atmosphere.
- the breaking strengths of samples (American Society for Testing and Materials, Philadelphia, Pa., test method ASTM Designation D-1682-64) before and after photolysis for one hour were as follows: acrylated cotton fabric, degree of substitution 0.28, 25 pounds (before) and 21 pounds (after); methacrylated cotton fabric, degree of substitution 0.15, 25 pounds (before) and 24 pounds (after).
- methacrylated cotton printcloth fabrics (degrees of substitution 0.00, 0.06, 0.09, 0.11, 0.27, and 0.36) were padded with N,N-dimethylformamide, N,N-dimethylformamide (90%)--water (10%), or N,N-dimethylformamide (67%)--water (33%) were photolyzed for 60 minutes as shown in Examples 2, 32, 34, 36, 38, 40, 44, 46, 48, 50, and 52 and their wrinkle recovery angles were compared with those of unphotolyzed cotton fabrics as shown in Examples 1, 31, 33, 35, 37, 39, 43, 45, 47, 49, and 51.
- the wrinkle recovery angles (wet) of the methacrylated fabrics photolyzed wet with N,N-dimethylformamide increased from 182° to 291° with increase in degrees of substitution from 0.00 to 0.36 as shown in Examples 1, 2, and 31-40.
- acrylated cotton printcloth fabrics (degrees of substitution 0.17, 0.28, and 0.41) were padded with N,N-dimethylformamide containing 0 to 4 percent acrylamide or with water containing 0 to 4 percent acrylamide and were photolyzed for 1 to 22 hours, as shown in Examples 53-73.
- Examples 53-55, 56-58, 59-61, 62-64, 65-67, 68, 69, 72, and 73 with Examples 27-30, respectively.
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Materials Engineering (AREA)
- Biochemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Toxicology (AREA)
- Textile Engineering (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Abstract
Acrylated cotton fabric is reacted with water-N,N-dimethylformamide solutions of acrylamide and then exposed to near ultraviolet light in an inert atmosphere to produce crosslinked acrylated cotton fabrics with durable press properties. The treatment is also applicable to methacrylated cotton fabric and the results obtained are similar.
Description
This invention relates to chemical processing of cotton textiles. Specifically, this invention relates to the wet-processing of cotton fabric which has been previously chemically modified. More specifically, this invention relates to a multistep wet processing of acrylated and methacrylated cotton fabric subjecting the reacted fabric to a near ultraviolet light treatment, a photofinishing step, to form a crosslinked cotton fabric with useful durable-press properties.
The main object of this invention is to provide a new textile wet-process method.
A second object of this invention is to provide a chemical treatment for further enhancing the physical properties of acrylated and methacrylated cotton without using a heat cure.
A third object of this invention is to provide a photofinishing process for initiating crosslinking reactions of acrylated and methacrylated cottons to yield textile fabrics with durable-press properties.
Developments in the commercial use of durable-press textiles have generally led to the use of blends of cotton fibers and man-made chemical fibers in order to have products with high wrinkle recovery angles and easy care properties. When all-cotton fabrics are finished by normally used processes chemical reagents are padded onto the fabrics; then they are cured by chemical catalyst and baking at a high temperature in an air oven. Usually, there is no reaction control, that is, directed selectivity of the reactions, in these processes. All-cotton products treated in this manner may have increased wrinkle recovery angles, but drastic and prohibitive losses in tearing and breaking strengths of the fabrics may occur during the curing steps. Similarly, a combination of chemical catalyst and baking at high temperature in one step and subsequent use of high energy radiation in a second step has been proposed for preparation of durable-press cotton products. These types of processes usually compound the drastic and prohibitive losses in breaking strengths of the cotton fabrics, first in the chemical catalyst-heat curing step and second in the high energy radiation step. Also, there is little or no reaction control, that is, directed selectivity of the reactions, in these processes.
By the process of the present invention the macromolecular properties of cotton are stabilized and the morphological properties of cotton are imparted a retention and recovery of initial shape and form after deformation, so that durable-press cotton fabric with high wrinkle recovery angles are produced. The method of this invention has as its objective the modification of the chemical structure of cotton fibers, mechanically organized into textile products and then the photofinishing of the modified products to yield an all-cotton, durable-press textile with high wrinkle recovery angles and easy care properties.
The instant invention defines a distinct improvement in the textile, durable-press properties of all-cotton fabrics in which acrylate and methacrylate chemical derivatives of cotton cellulose fabrics are prepared and then photolyzed by near ultraviolet light to yield crosslinked, durable-press cotton fabrics with improved wrinkle recovery angles with minimum losses in breaking strengths of the chemically modified cotton fabrics. Cotton cellulose fabrics that had been chemically modified by reaction with acryloyl chloride or methacryloyl chloride to degrees of substitution ranging from 0.08 to 0.50 were padded with N,N-dimethylformamide, water, combinations of these two solvents ranging from 10 to 100 percent N,N-dimethylformamide and 10 to 100 percent water, or solutions of these solvents containing acrylamide ranging from 0.5 to 4 percent and then photolyzed for 30 minutes to 22 hours in nitrogen or air atmospheres at ambient temperature, about 48° C, by near ultraviolet light with a wavelength maximum of 3500 angstroms, which had been shown to yield a maximum concentration of cellulosic radicals with minimum degradative damage to the physical properties of cotton, to yield cotton fabrics with Monsanto wrinkle recovery angles (American Society for Testing and Materials, Philadelphia, Pa., test method ASTM Designation D1295-60T) as high as 331° (wet) and 285° (conditioned), as compared with wrinkle recovery angles of control fabrics of 174° (wet) and 160° (conditioned).
Samples of cotton fabric used were a commercial grey printcloth (about 3.2 ounces per square yard, 80 × 80 thread count) which had been enzymatically desired, alkali scoured, and peroxide bleached before use. Typically, two or three strips of cotton fabric about 5 to 7.5 parts, were rolled together and placed together in a container fitted with a drying tube. Calcium carbonate (about 6 parts), N,N-dimethylformamide (about 60 parts), and acryloyl chloride or methacryloyl chloride (3 to 10 parts) were added to the container. The container and its contents were heated typically in an oil bath at 100° to 110° C for the time required to give the cotton cellulose ester with the desired degree of substitution. After cooling the samples to about 25° C, they were washed in water and air-dried either in a slack condition or under tension on pin frames.
The present invention can best be described as the acrylated and the methacrylated cotton products and processes for making these, the processes of which can be that embodiment for imparting to cotton fabrics the desirable durable press property of wrinkle recovery while retaining the natural properties of untreated cotton, and comprising:
(a) impregnating either the acrylated cotton fabric or the methacrylated cotton fabric of a degree of substitution of about from 0.08 to 0.5, with a 0.5 to 4.0% acrylamide solution in a solvent mixture of water and N,N-dimethylformamide wherein the water content can vary from 10 to 100%, and vice versa,
(b) subjecting the wet impregnated acrylated or methacrylated cotton fabric to a photolyzing treatment consisting of exposing the impregnated fabric to near ultraviolet light (ordinarily in the range of about from 3100 to 4000 Angstrom units of intensity, the maximum intensity generally peaking at about 3500 Angstroms) for about from 30 minutes to 22 hours, in an inert atmosphere, generally nitrogen, to initiate a free radical crosslinking reaction between substituted acrylate groups or methacrylate groups on cotton as well as substituted acrylate or methacrylate groups and cotton to obtain a crosslinked, durable-press fabric, which is generally washed and dried before fabrication of a garment or other finished product.
The following samples are provided to facilitate the comprehension of this invention and should not be construed as limiting the invention in any manner whatever.
Seventy-three samples were prepared for a comprehensive study of the effects observed when practicing this invention. Samples of the acrylated or methacrylated cotton fabrics were impregnated with solvents or solutions, as indicated by padding to a wet add-on of about 180 percent. These treated samples were placed in a container in the desired atmosphere and exposed to near ultraviolet light which had about 90 percent of the intensity of the light with a wavelength of about 3500 Angstrom units, at ambient temperatures for certain specific times, ranging about from 30 minutes to 22 hours, in a nitrogen atmosphere. Typically, the breaking strengths of samples (American Society for Testing and Materials, Philadelphia, Pa., test method ASTM Designation D-1682-64) before and after photolysis for one hour were as follows: acrylated cotton fabric, degree of substitution 0.28, 25 pounds (before) and 21 pounds (after); methacrylated cotton fabric, degree of substitution 0.15, 25 pounds (before) and 24 pounds (after).
______________________________________
Effects of Degree of Substitution, Solvent, and Time of
Photolysis on the Wrinkle Recovery Angles of Acrylated and
Methacrylated Cotton Fabrics
Degree Time of
of sub- photo- Wrinkle recovery
stitu- lysis,.sup.b
angle (W+F), degrees
Ex. tion Solvent.sup.a
min Wet Conditioned
______________________________________
Control cotton fabric
1 0.00 DMF 0 174 160
2 0.00 DMF 60 182 165
Acrylated cotton fabric
3 0.08 DMF 0 171 168
4 0.08 DMF 60 236 177
5 0.12 DMF 0 160 175
6 0.12 DMF 60 250 190
7 0.16 DMF 0 190 184
8 0.16 DMF 60 277 223
9 0.29 DMF 0 181 184
10 0.29 DMF 60 285 217
11 0.35 DMF 0 189 203
12 0.35 DMF 30 260 207
13 0.35 DMF 60 292 229
14 0.35 DMF 120 285 219
15 0.50 DMF 0 181 201
16 0.50 DMF 60 296 225
17 0.16 10% aq. DMF 0 190 184
18 0.16 10% aq. DMF 60 277 214
19 0.16 33% aq. DMF 0 190 184
20 0.16 33% aq. DMF 60 283 214
21 0.41 10% aq. DMF 0 185 179
22 0.41 10% aq. DMF 30 261 222
23 0.41 10% aq. DMF 60 281 227
24 0.41 10% aq. DMF 120 303 219
25 0.50 33% aq. DMF 0 181 201
26 0.50 33% aq. DMF 60 290 219
27 0.29 water 0 181 184
28 0.29 water 60 225 215
29 0.50 water 0 181 201
30 0.50 water 60 228 217
Methacrylated cotton fabric
31 0.06 DMF 0 171 184
32 0.06 DMF 60 224 190
33 0.09 DMF 0 163 174
34 0.09 DMF 60 239 187
35 0.11 DMF 0 189 193
36 0.11 DMF 60 286 235
37 0.27 DMF 0 171 181
38 0.27 DMF 60 291 195
39 0.36 DMF 0 162 180
40 0.36 DMF 60 277 212
41 0.36 DMF.sup.c/ 0 162 180
42 0.36 DMF.sup.c/ 60 177 181
43 0.09 10% aq. DMF 0 163 174
44 0.09 10% aq. DMF 60 203 187
45 0.09 33% aq. DMF 0 163 174
46 0.09 33% aq. DMF 60 205 188
47 0.27 10% aq. DMF 0 171 181
48 0.27 10% aq. DMF 60 291 212
49 0.27 33% aq. DMF 0 171 181
50 0.27 33% aq. DMF 60 295 224
51 0.36 10% aq. DMF 0 162 180
52 0.36 10% aq. DMF 60 290 211
______________________________________
.sup.a/ DMF = N,N-dimethylformamide.
.sup.b/ Photolyzed in nitrogen atmosphere at 40° C by 3100-4000 A.
peak 3500 A., light.
.sup.c/ Photolyzed in air.
______________________________________
Effects of Addition of Acrylamide to Solvent
on the Wrinkle Recovery Angles of Photolyzed
Acrylated Cotton Fabrics.sup.a/
Monomer Wrinkle recovery angle
concentration,
(W+F), degrees
Example
Solvent.sup.b/
% Wet Conditioned
______________________________________
Degree of substitution: 0.17
53 DMF -- 279 218
54 DMF 2 268 202
55 DMF 4 300 178
56 H.sub.2 O -- 221 186
57 H.sub.2 O 2 292 218
58 H.sub.2 O 4 310 220
Degree of substitution: 0.28
59 DMF -- 285 217
60 DMF 2 311 217
61 DMF 4 302 213
62 H.sub.2 O 1 279 234
63 H.sub.2 O 2 290 246
64 H.sub.2 O 4 291 217
Degree of substitution: 0.41
65 DMF -- 306 218
66 DMF 2 299 206
67 DMF 4 313 198
68 H.sub.2 O 0.5 289 260
69 H.sub.2 O 1 297 261
70 H.sub.2 O 1 301.sup.c/
248.sup.c/
71 H.sub.2 O 1 331.sup.d/
285.sup.d/
72 H.sub.2 O 2 299 264
73 H.sub.2 O 4 308 257
______________________________________
.sup.a/ Samples of fabric padded to about 180% wet add-on; photolyzed at
40° C by 3100-4000 A., peak 3500 A., light for 1 hr.; then washed
and air-dried.
.sup.b/ DMF = N,N-dimethylformamide.
.sup.c/ Photolyzed for 3 hr.
.sup.d/ Photolyzed for 22 hr.
By the method as described in the specification above, acrylated cotton printcloth fabrics (degrees of substitution 0.00, 0.08, 0.12, 0.16, 0.29, 0.35, 0.41, and 0.50) were padded with N,N-dimethylformamide, water, N,N-dimethylformamide
(90%)--water (10%), or N,N-dimethylformamide (67%)-- water (33%) were photolyzed for 60 minutes as shown in Examples 2, 4, 6, 8, 10, 13, 16, 18, 20, 23, 26, 28, and 30 and their wrinkle recovery angles were compared with those of unphotolyzed cotton fabrics as shown in Examples 1, 3, 5, 7, 9, 11, 15, 17, 19, 21, 25, 27, and 29. The wrinkle recovery angles (wet) of the acrylated fabrics photolyzed wet with N,N-dimethylformamide increased from 182° to 296° with increase in degrees of substitution from 0.00 to 0.50 as shown in Examples 1-11, 13, 15, 16. Acrylated fabric samples wet with water and photolyzed exhibited much lower increases in wrinkle recovery angles as shown in Examples 27-30. Acrylated samples wet with N,N-dimethylformamide (90%)-- water (10%), as shown in Examples 17, 18, 21, and 23, or N,N-dimethylformamide (67%)--water (33%), as shown in Examples 19, 20, 25, and 26, and photolyzed showed increases in wrinkle recovery angles (wet) similar to those shown when acrylated fabrics were wet with N,N-dimethylformamide and photolyzed. The effects of time of photolysis on the wrinkle recovery angles of acrylated fabrics are shown in Examples 11-14 and 21-24 with times of photolysis ranging from 0 to 120 minutes. The major increases in wrinkle recovery angles of the fabrics had occurred after 60 minutes of photolysis.
By the method as described in the specification above, methacrylated cotton printcloth fabrics (degrees of substitution 0.00, 0.06, 0.09, 0.11, 0.27, and 0.36) were padded with N,N-dimethylformamide, N,N-dimethylformamide (90%)--water (10%), or N,N-dimethylformamide (67%)--water (33%) were photolyzed for 60 minutes as shown in Examples 2, 32, 34, 36, 38, 40, 44, 46, 48, 50, and 52 and their wrinkle recovery angles were compared with those of unphotolyzed cotton fabrics as shown in Examples 1, 31, 33, 35, 37, 39, 43, 45, 47, 49, and 51. The wrinkle recovery angles (wet) of the methacrylated fabrics photolyzed wet with N,N-dimethylformamide increased from 182° to 291° with increase in degrees of substitution from 0.00 to 0.36 as shown in Examples 1, 2, and 31-40. Photolyzed methacrylated samples (degrees of substitution 0.09 to 0.36 wet with N,N-dimethylformamide (90%)--water (10%), as shown in Examples 43, 44, 47, 48, 51, and 52, had wrinkle recovery angles (wet) of 203° to 291°. Photolyzed methacrylated samples (degrees of substitution 0.09 to 0.27) wet with N,N-dimethylformamide (67%)--water (33%), as shown in Examples 45, 46, 49, and 50, had wrinkle recovery angles (wet) of 205° to 295°.
When the method as described in the specification above was changed so that the esterified fabrics were photolyzed in air rather than in nitrogen, increased in wrinkle recovery angles of the photolyzed, esterified fabrics over those of unphotolyzed fabrics were not obtained, as shown in Examples 41 and 42.
By the method as described in the specification above, acrylated cotton printcloth fabrics (degrees of substitution 0.17, 0.28, and 0.41) were padded with N,N-dimethylformamide containing 0 to 4 percent acrylamide or with water containing 0 to 4 percent acrylamide and were photolyzed for 1 to 22 hours, as shown in Examples 53-73. Photolyzed acrylated fabrics wet with water and acrylamide had higher wrinkle recovery angles than photolyzed acrylated fabrics wet with water alone; or with N,N-dimethylformamide and acrylamide. Compare Examples 53-55, 56-58, 59-61, 62-64, 65-67, 68, 69, 72, and 73 with Examples 27-30, respectively. Acrylated fabrics, degree of substitution 0.41, wet with water containing 0.5 to 4 percent acrylamide and photolyzed for 1 to 22 hours had wrinkle recovery angles (wet) as high as 331° and wrinkle recovery angles (conditioned) as high as 285°, as shown in Examples 68-73.
Claims (4)
1. A process for imparting to cotton fabrics the desirable durable-press property of wrinkle recovery while retaining the natural properties of untreated cotton, the process comprising:
(a) impregnating an acrylated cotton fabric of about from 0.08 to 0.5 degree of substitution with a 0.5 to 4.0% acrylamide solution in a solvent mixture of water and N,N-dimethylformamide wherein the water content or the N,N-dimethylformamide content can vary from 10 to 100%,
(b) subjecting the wet impregnated acrylated cotton fabric of (a) to a photolyzing treatment consisting of exposing the impregnated fabric to near ultraviolet light of 3100 to 4000 Angstrom units, with maximum intensity of about 3500 Angstrom units, for about from 30 minutes to 22 hours, in an inert atmosphere to initiate a free-radical crosslinking reaction between substituted acrylate groups on cotton as well as substituted acrylate groups and cotton to obtain a crosslinked, durable-press fabric, and
(c) washing and drying the photolyzed acrylated and crosslinked fabric.
2. The photolyzed acrylated and crosslinked fabric produced by the process of claim 1.
3. A process for imparting to cotton fabrics the desirable durable-press property of wrinkle recovery while retaining the natural properties of untreated cotton, the process comprising:
(a) impregnating a methacrylated cotton fabric of about from 0.06 to 0.36 degree of substitution in a solvent mixture of water and N,N-dimethylformamide wherein the water content or the N,N-dimethylformamide content can vary from 10 to 100%,
(b) subjecting the wet impregnated methacrylated cotton fabric of (a) to a photolyzing treatment consisting of exposing the impregnated fabric to near ultraviolet light of 3100 to 4000 Angstrom units, with maximum intensity of about 3500 Angstrom units, for about 60 minutes, in an inert atmostphere to initiate a free-radical crosslinking reaction between substituted methacryate groups on cotton as well as substituted methacrylate groups and cotton to obtain a crosslinked, durable-press fabric, and
(c) washing and drying the photolyzed methacrylated and crosslinked fabric.
4. The photolyzed methacrylated and crosslinked fabric produced by the process of claim 3.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/563,257 US4108748A (en) | 1975-03-28 | 1975-03-28 | Photofinishing of cotton textiles |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/563,257 US4108748A (en) | 1975-03-28 | 1975-03-28 | Photofinishing of cotton textiles |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US4108748A true US4108748A (en) | 1978-08-22 |
Family
ID=24249765
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US05/563,257 Expired - Lifetime US4108748A (en) | 1975-03-28 | 1975-03-28 | Photofinishing of cotton textiles |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US4108748A (en) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4253841A (en) * | 1979-02-23 | 1981-03-03 | The United States Of America As Represented By The Secretary Of Agriculture | Process for photoinitiated, polymeric encapsulation of cotton fibers in durable-press textiles |
| US4336023A (en) * | 1980-12-30 | 1982-06-22 | Rohm And Haas Company | Formaldehyde-free durable press finish fabrics |
| US4764395A (en) * | 1985-11-06 | 1988-08-16 | Ciba-Geigy Corporation | Process for finishing a textile fabric with a radiation crosslinkable compound |
| US5459301A (en) * | 1993-03-04 | 1995-10-17 | Miller; Alan E. | Cyclic microwave treatment of pressed garments |
| GB2366568A (en) * | 2000-09-01 | 2002-03-13 | Unilever Plc | Method of treating fabric |
| US6436484B1 (en) | 1997-12-09 | 2002-08-20 | Coats American, Inc. | Processes for coating sewing thread |
| US6488718B1 (en) | 1998-11-13 | 2002-12-03 | Cotton Incorporated | Methods for reducing the flammability of cellulosic substrates |
| US6491727B1 (en) | 1999-06-09 | 2002-12-10 | Cotton Incorporated | Methods for reducing the flammability of cellulosic substrates |
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Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4253841A (en) * | 1979-02-23 | 1981-03-03 | The United States Of America As Represented By The Secretary Of Agriculture | Process for photoinitiated, polymeric encapsulation of cotton fibers in durable-press textiles |
| US4336023A (en) * | 1980-12-30 | 1982-06-22 | Rohm And Haas Company | Formaldehyde-free durable press finish fabrics |
| US4764395A (en) * | 1985-11-06 | 1988-08-16 | Ciba-Geigy Corporation | Process for finishing a textile fabric with a radiation crosslinkable compound |
| US5459301A (en) * | 1993-03-04 | 1995-10-17 | Miller; Alan E. | Cyclic microwave treatment of pressed garments |
| US6436484B1 (en) | 1997-12-09 | 2002-08-20 | Coats American, Inc. | Processes for coating sewing thread |
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| US6828023B2 (en) | 1997-12-09 | 2004-12-07 | Coats American, Inc. | Coated sewing thread |
| US6488718B1 (en) | 1998-11-13 | 2002-12-03 | Cotton Incorporated | Methods for reducing the flammability of cellulosic substrates |
| US6491727B1 (en) | 1999-06-09 | 2002-12-10 | Cotton Incorporated | Methods for reducing the flammability of cellulosic substrates |
| GB2366568A (en) * | 2000-09-01 | 2002-03-13 | Unilever Plc | Method of treating fabric |
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